


How to Secretly Date Your College Professor

by DeansDirtyLittleSecret



Series: Professor Dean Winchester AU [3]
Category: Supernatural
Genre: Alternate Universe - College/University, Angst, Drinking, Explicit Language, Explicit Sexual Content, F/M, Hangover, Jealous Reader, Misinterpretation of Certain Events, Originally Posted on Tumblr, Professor Dean Winchester, Reader-Insert, Smut
Language: English
Status: Completed
Published: 2015-07-17
Updated: 2015-07-17
Packaged: 2018-04-09 20:53:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,433
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4363859
Author URL: https://archiveofourown.org/users/DeansDirtyLittleSecret/pseuds/DeansDirtyLittleSecret
Summary: <blockquote class="userstuff">
              <p>Dating your professor is hard. It should come with an instruction manual.</p>
            </blockquote>





	How to Secretly Date Your College Professor

**Author's Note:**

> Every good story needs conflict, right?

_ How to Secretly Date Your College Professor: _

  1. _Just because you're sleeping with the teacher doesn't mean you can be late to class._

  2. _Don't expect special favors._

  3. _You will get jealous but you can't show it. Secret relationship, remember?_

  4. _Drinking and jealousy don't mix. Oh, and Tylenol doesn't always help hangovers._

  5. _A watched cell phone doesn't ring._

  6. _Sometimes what you see is not what you get._

  7. _Making up is fun to do._




* * *

 

You heard the shower turn off just as you slipped your shirt over your head. Dean walked out of the bathroom a few minutes later, a towel around his waist, his hair still wet and dripping slightly on his broad shoulders.

“Hey, are you leaving?” he asked. He kept one hand on the towel as he rifled through the top drawer of his tiny dresser, slamming it shut with his elbow once he had his boxer briefs in his hand.

“Yeah,” you replied. You finished tying your shoe, then stood up, your eyes darting around the room, trying to remember where you’d dropped your backpack the night before.

“Downstairs,” Dean said. “On the coffee table.” He put his hand on your waist, smiling as he leaned in for a kiss.

You returned the smile and the kiss, resisting the urge to yank the towel off of him and push him down on the bed. You needed to get back to the dorm, shower and change your clothes before your first class. You broke off the kiss and patted him on the cheek.

“If you hurry, you can tell me goodbye,” you said as you walked out of his room and down the stairs of the small house Dean had rented just a few miles from school. You grabbed your backpack from the coffee table, opening it and pulling out the teaching assistant application as you stepped into the kitchen. You set it under Dean’s car keys, then you pulled a bottle of orange juice from the fridge, popped off the lid and stood by the sink staring out the window. It wasn’t more than a few minutes before you felt strong arms slide around your waist and a nose bury itself in your hair, inhaling deeply. You let yourself relax into his arms, the only place you wanted to be. You didn’t want to leave.

“I’m sorry,” he murmured, his lips sliding over your neck.

“I know,” you answered. Dean was always sorry, it seemed to be the only thing he’d been able to say over the last two weeks, since the first time you’d had sex in his office. He was sorry you couldn’t go on a real date; sorry you had to sneak in and out of his house through the back door; sorry he couldn’t call, just text; sorry you couldn’t walk into class together as a couple; sorry, sorry, sorry, sorry. You’d heard him apologize more since that day than you’d heard anyone apologize your entire life.

You turned in his arms, sighing dramatically. “Jesus, Professor Winchester,” you mumbled. “Enough apologizing.” You wrapped your hands around his neck and pulled him down into a long, deep kiss. “I have to go. I left you something.” You pulled yourself free of his embrace, snatched your backpack off the counter where you’d set it and slipped out the back door. You could feel Dean’s eyes on you as you hurried across the lawn and out the side gate. All of this sneaking around crap was playing a toll on both of you.

Your car was parked a couple of blocks over, next to a little playground. You pulled your sweater tight around yourself, shivering in the cool morning air. You unlocked your car and slipped inside, glancing at the clock when the engine turned over. You had just a little over an hour before your first class.

* * *

You’d been running late all day, ever since leaving Dean’s house. You’d had to go to your first class with wet hair, you’d left your Latin paper on the desk in your dorm room so you hadn’t had time to eat lunch because you had to go back for it, and then to top it all off, you’d locked your keys in your room and it had taken the RA far longer than necessary to unlock it for you, making you twenty minutes late for Dean’s class. When you finally slid into a seat in the back row, you were tired and irritable. The disapproving look Dean shot your direction didn’t help.

You ignored him, slouched in your seat and pulled your notebook from your bag. You hurried to scribble the notes from the board while you also listened to his lecture. You could feel a headache forming right behind your eyes. Your phone vibrated in your back pocket, startling you. You yanked it free and set it on your desk behind the edge of your book. It was Jo.

Jo:  You in class?

You:  Yeah. Winchester’s. Why

Jo:  I’ll meet you after.

Great, that was just what you needed. You liked Jo well enough, but she could be tiresome. You’d been friends since freshman year, but you hadn’t been close for the last couple of years, since you’d forced yourself to buckle down and get through school, and Jo had chosen the party girl route, barely scraping by because she worried too much about when and where her next date was coming from and if there was a party she could go to. You sighed inwardly. This day just kept getting better and better.

“Ms. Y/L/N, could you see me after class?” Dean said from the front of the room. You’d been so caught up in your own thoughts that you hadn’t even realized class was over.

“Yes, Professor,” you mumbled. You shoved your things in your bag and made your way through the crowd of students leaving the room to the desk down in the front. Dean smiled at you, winking subtly.

“You okay?” he said quietly, doing his best to keep the conversation between the two of you. Once the door closed behind the last student, Dean stepped closer to you, his hand out to put it on your waist, but you took a step back, your heart clenching at the confused look on his face.

“Sorry,” you whispered. “Jo’s meeting me.” You shrugged apologetically.

Dean nodded his understanding, stepping back and sitting on the edge of his desk. “You turned in an application for my teaching assistant,” he said matter-of-factly. “I’m not sure what to do with that.”

“Read it,” you muttered angrily. You hadn't expected this.

“It might not be a good idea for you to be my TA,” he said. “It might not look good if I give it to you. It could bring up a lot of questions we don’t want to answer.”

“But I’m probably the most qualified,” you interrupted. “My grades, my major, all of that should be taken into consideration. Not the fact that I’m fucking the professor, which I thought was just between you and I anyway.”

The look on Dean's face made you immediately regret your harsh words, but before you could say anything, the door at the top of the stairs opened. You glanced over your shoulder to see Jo waiting for you. Unsure exactly what to do or even what to say, you hefted your bag higher on your shoulder, turned and ran up the stairs and out the door, smiling uneasily at your friend. Maybe she’d go get a drink with you. You could definitely use one.

* * *

Jo was more than happy to get a drink with you, even offering to pay for the first round. You slumped in the booth, mulling over what you’d said to Dean. You couldn’t stop thinking about the pained expression he’d been wearing when you’d walked away from him.

You took your phone out several times, intent on texting him and apologizing, but you weren’t even sure where to start. After pulling it out of your pocket for the third time, you put it away, deciding to apologize later. Jo came back from the bar, more drinks, french fries and nachos in hand. She dropped into the seat opposite you, smiling.

“So, my brother just texted me,” she chirped. “I guess Professor Winchester had a shitty day, so Sam’s bringing him out for drinks. I’m so going to make my move.”

You forced yourself not to reach across the table and slap Jo, after all she had no idea what was going on between you and her brother’s friend, though that didn’t change the irritation you felt or the jealousy needling its way into the pit of your stomach.

“I thought Sam said the professor was involved with someone,” you said, faking calm.

“Never stopped me before,” Jo grinned, downing one of the shots she’d brought to the table.

“Excuse me a minute,” you grumbled, stumbling out of the booth and practically running to the bathroom.

You stayed in the bathroom until your phone vibrated in your pocket, Jo insisting you come back to the table now. You took a deep breath, steeling yourself against the mess you were about to walk into. You just needed to get through an hour or two and then you’d make your escape.

You could hear Jo’s laughter floating through the bar as you weaved through the Friday night crowd back to your table. Jo’s brother was there, along with Dean, his over six foot body shoved into the booth beside Jo, who was already draped all over him, her blonde hair flipped over her shoulder and her brown eyes staring adoringly at him. You recognized the look immediately, you’d seen it at least a dozen times before, it was her ‘I’m available’ look and it almost always worked. You felt almost dizzy with despair.

You plastered a fake smile on your face as slid into the booth. “Hi,” you managed to spit out, refusing to make eye contact with anyone at the table.

Sam, Jo’s brother, greeted you with a quick bump to the shoulder, nearly sending you to the floor. You laughed half-heartedly and bumped him back. When you did finally look at Dean, he was smiling at you hopefully, his attentions on you, not Jo, despite the arm she had casually resting on the seat behind him, the hand clutching his bicep or the fact that her body was almost flush against his.

“God, Y/N, I thought you died in there,” Jo yelled over the music.

“Long line,” you mumbled.

“Dean, you know Y/N, right?” Jo continued like she wasn’t really listening to you.

“She’s in one of my classes,” Dean said, his eyes boring into yours. “You applied for the TA position, right?”

You nodded weakly. You hated this. It was bad enough that the two of you had to act like you were practically strangers, but knowing that you’d argued the last time you’d seen him didn’t help. You rubbed a hand over your face, trying to keep it together. You grabbed a shot off of the tray in the middle of the table, downing it in one swallow. You tried not to stare at Jo’s hand on Dean’s arm.

* * *

Two hours later you were watching Sam and Dean play pool. The four of you had moved to a table in the corner by the billiard tables, the stool you were sitting on was leaning against the wall and your feet were propped on the stool Jo had yet to sit on. She was too busy following Dean around the table, one hip propped against it whenever he took a shot, laughing, giggling, and finding any excuse to touch him. She was in full flirt mode, laying it in thick. It made you want to throw up.

Dean had tried to talk to you a couple of times, but had given up when it became clear Jo wasn't going to let that happen. Concerned that Jo would suspect something, he'd ended up avoiding you as much as possible and you’d done the same thing with him. All you wanted to do was throw yourself in his arms and apologize for your earlier behavior, but instead you were knocking back drink after drink, hoping to obliterate the sight of Jo hanging all over him from your mind.

When Jo stood on her toes and whispered something in Dean’s ear, a tiny smile on her face, you realized you’d had enough. You pushed yourself to your feet. “I’m going to take off,” you said, directing your words at Dean, though you were looking at Jo. “I’ve had enough fun for one night.” You picked up your purse and headed for the door, not glancing back.

The cool fall air felt good on your overheated skin. You leaned against the wall outside the door for a minute to catch your breath, pulling your car keys from your purse. You tried to push yourself away from the wall but a wave of dizziness hit you.

“Shit,” you mumbled to yourself, falling back against the wall.

“Give me those,” Dean said, pulling your keys from your hand. He must have followed you out of the bar.

“Hey,” you protested meekly. “How am I supposed to get home without those?”

“You are not driving,” he said.

The bar door opened behind him, Jo’s pretty blonde head popping out. “Hey, it’s your turn,” she said. She shot you a dirty look when Dean turned to look at her.

Dean smiled at her. You immediately recognized it as his patient Professor Winchester look, one he reserved for students who were starting to get on his nerves. “I think I’m going to drive Y/N home,” he said. “Tell Sam goodbye for me.”

Jo stepped out the door, a pissed look on her face. “I’ll take her back to her dorm. You stay here with my brother. I’ll be back in like, twenty minutes.”

Dean shook his head, taking a hold of your elbow. “Thanks Jo,” he said. “But I’ve had enough for one night.” He steered you away from the bar toward his 1967 black Chevy Impala, opened the door and helped you inside. You heard him tell Jo goodbye before he climbed in the driver’s side and slammed the door.

“Are sure you don’t want to stay here with Jo?” you said. “I could call a cab.”

“I’m going to pretend you didn’t say that,” he murmured patiently, starting the car. “What the hell was that back there anyway, Y/N?”

“It’s called jealousy, Professor Winchester,” you snapped. You put your head in your hand, rubbing the spot on your forehead just above your eyes. You could already feel a headache coming on. “It’s what happens when your boyfriend spends the evening pawing another girl right in front of you. Oh wait, I’m sorry, I can’t call you that, can I? I guess I should have said the teacher you’re secretly screwing.”

Out of the corner of your eye you could see Dean’s mouth open, then snap shut. He pulled his lower lip between his teeth, his brow furrowed, his grip on the steering wheel so tight his knuckles were turning white.

You shot a look at the streets flashing by. “Where are we going?” you muttered.

"To your dorm," he growled.

“We're not going back to your place?" you whispered. You'd assumed when he'd offered to take you home that he'd meant his home. You'd obviously been wrong.

"No," Dean said angrily.

You waited for more of an explanation, but the car was quiet except for the classic rock station on the radio. Dean didn’t say another word until he pulled to a stop in front of your building.

"Drink some water, take a couple of Tylenol," he murmured. "It'll help." He didn’t even look at you as he spoke.

You stared helplessly at him for longer than was comfortable for either of you, then wordlessly stepped out, the heavy door creaking loudly as you closed it.

Dean pulled out of the lot without so much as a glance back, engine revving, tires squealing.

Your heart ached as you watched him drive away. You forced yourself to go inside, clumsily swiping your keycard to open the door and staggering to the elevator. You counted backwards from one hundred as it took you upstairs, praying you wouldn't puke. You frantically unlocked your room, barely making it to the bathroom before hitting your knees, your head in the toilet. The last thing you remembered was the feel of the cold porcelain against your cheek before your eyes closed and you slipped into blessed unconsciousness.

* * *

 

You came awake curled up in the fetal position on your bathroom floor. A pair of your sweatpants was under your head and a towel covered you from shoulder to waist, not that you remembered grabbing either of them.. You were stiff, sore and your head was pounding. As you sat up, another wave of nausea washed over you and you remembered why you’d promised yourself you wouldn’t drink this year. You waited a minute for it to pass, then you pushed yourself to your feet, mumbling ‘damn it’ under your breath every time the room started to spin and you had to put a hand out to steady yourself.

Once you were on your feet, you dug through the medicine cabinet over the sink and grabbed the bottle of Extra Strength Tylenol you kept in there, then you made your way out of the bathroom and across the room to the small refrigerator in the corner, pulling out a bottle of water. You managed to swallow two of the tiny white pills, grimacing at the feel of them sliding down your raw throat. You closed the blinds and dropped to your bed, never more grateful than you were now that you didn’t have a roommate.

The vibration of your cell phone from your back pocket startled you; you’d forgotten it was even in there. You yanked it out, nearly dropping it on the floor, more than ready to beg for Dean’s forgiveness. But it was Jo.

You hit ignore, then you thumbed through the phone to see what you’d missed while you’d slept on the bathroom floor. Multiple calls and texts from Jo, a text from your mom and one from your sister in New York, but nothing from Dean. You pulled his name up in your contact list, your finger hovering over the ‘call’ symbol. Instead, you hit the message button and quickly typed “I’m sorry.” You hit send before you could change your mind.

* * *

 

Monday seemed to take forever to come around. You spent all day Saturday laying in bed, head pounding, room spinning, drifting in and out of sleep, the Tylenol you'd taken completely useless. It wasn’t until late in the afternoon that you were able to drag yourself out of bed and down to the student union for food, putting yourself in a quiet corner and working your way through a bowl of soup and a glass of 7-Up. You avoided everybody, managing to make it back to your room without having to interact with any of your fellow classmates. You stayed in your room on Sunday, watching television and trying to catch up on your neglected school work. Sunday afternoon you got your RA to give you a ride to the bar to pick up your car, knowing she wouldn’t ask a lot of questions.   

You hadn’t spoken to Jo all weekend, purposely ignoring her. She’d sent you at least a dozen frantic text messages Friday night and early Saturday morning, all of them asking about Dean. She’d tried calling several times, but you didn’t answer. The only call you cared about never came. The one from Dean.

You actually felt normal by the time your first class rolled around on Monday. Normal and slightly anxious. You weren’t exactly sure what was going to happen when you saw Dean, but you were ready to find out. The only contact over the weekend had been a group email to all of the TA applicants telling them to be prepared to interview Monday night after his last class.

You tried to get to his class early, but a frantic call from a member of your study group waylaid those plans and kept you busy right up until class started. You slid into a desk in the back row with about five minutes to spare.

Dean didn't make eye contact with you once, in fact, he seemed to be trying extra hard to not look at you. Even when he announced the teaching assistant interview times for that evening, his eyes never strayed your direction. Yours was the last of the evening. You hoped that was a good thing.

You didn't even get a chance to talk to him after class dismissed; he'd scheduled the interviews to start right away. Since you had almost two hours to waste before your interview started, you wandered down to the library to study, though you spent most of the time rehearsing your apology to Dean in your head.

You found yourself standing in front of his classroom door ten minutes before your scheduled interview, heart pounding, palms sweating, stomach fluttering with nerves. You pushed open the door several inches, hoping to catch him alone.

Dean was sitting on the edge of his desk with Jo was standing in front of him, right between his legs, her hands on his thighs. She was leaning toward him and you were pretty goddamn sure they were about to kiss. You stepped back so fast that when you let go of the door, it closed with a loud thunk. You scurried down the hall, slipping into the shadows.

A few minutes later Jo emerged, clothes rumpled and in disarray. You bit your lip, fighting back tears, watching her as she seemingly floated down the hall in the opposite direction. You stepped out of the shadows, striding purposefully back to Dean's class. You'd made a mistake, a huge mistake.

You shoved open the door and ran right into Dean, catching him off guard.

"So, what?" you yelled. "I'm not the only student you're messing around with? I thought you weren't interested in Jo?"

"I'm not," Dean shot back. "What the hell are you talking about?"

"I saw you and her...You were kissing her and she was touching you..." you stammered.

"I didn't kiss her," Dean replied. He seemed genuinely confused. "And whatever you just saw, that was all her. I asked her to leave..."

"Yeah, right," you grumbled.

Dean took hold of your elbow, pulling you roughly against him. "Y/N, you are the only woman I want," he said. "Just you."

"But -" you protested.

You didn't get a chance to say anything else because Dean's mouth was on yours, swallowing your words. He cupped the back of your head, holding you close.

"Stop talking," he muttered. "Listen to me. It's you, Y/N, just you. I thought long and hard about you and I this weekend. I forced myself to take a step back and really look at this and you know what I decided. I want it, damn the consequences, damn everyone else. I want it. I want you. Do you understand me?"

You smiled, relief flooding you. "Yes," you nodded. "I understand."

Dean returned the smile, ducking his head to catch your lips in his. He kissed you, his body pressed against yours, his hands on your cheeks, his thumbs brushing away the tears you hadn't realized were there.

"I'm sorry," you murmured.

"So am I," he said.

Your bag dropped to the floor as Dean pushed at your clothes, his hands sliding beneath the thin sweater you were wearing and up your chest to cup your breast in his hand. He kneaded it roughly as he tugged at the conservative skirt you were wearing, pulling it up over your thigh as he shoved his hand between your legs and pushed aside your underwear. His middle finger dipped into your wet pussy, his thumb flicking at your clit.

"Professor Winchester," you moaned, grinding your hips down against his exploring fingers.

An almost feral growl rumbled out of his chest. "I need you to touch me, Y/N," he gasped.

You ran your hand over the front of Dean's dark khakis, his cock jumping at the attention. You deftly opened his pants, your hand slipping down the front of them to stroke him slowly, drawing another gasp from him.

Dean pushed your skirt up around your waist and your panties down your legs, then he slid his hands under your thighs and picked you up, holding you against the wall. He lowered you onto his throbbing cock, both of you moaning at the connection.

He moved, pulling out almost completely, before thrusting back into you, hard. He braced one hand on the wall by your head, his hips moving in a quick staccato, thrusting into you repeatedly.

You threw your head back, slamming it into the wall, as you felt the orgasm building deep in the pit of your stomach. Using the wall as leverage to hold you up, Dean slid his other hand between your bodies, easily finding and rubbing your clit, sending unbelievable heat barreling through you. He bit at your lip, sucking your tongue into his mouth, breathy gasps escaping his open mouth.

"Come on, baby, let me feel it," he whispered, his voice low and thick with lust.

You let go with a deep moan, your nails digging into the back of Dean's neck as the orgasm took over. Bright, white light filled your vision, your walls clenching around Dean. He thrust into you several more times, both of you clutching and clawing at each other as the pleasure consumed you.

As the earth shattering sensations started to fade, Dean set you on the floor, his body still flush against yours. He pulled your skirt down and fixed his own clothing. He kissed you, his lips moving tenderly over yours. When he eventually pulled away, it was like losing a part of yourself. He kept your fingers intertwined with his, bending over to retrieve your panties and your bag, handing them both to you.

He smiled at you, that sweet, yet somehow still cocky smile he had that turned your insides to jelly. He squeezed your hand and pressed a quick kiss to your forehead.

"Just you, Professor Winchester," you said.

"Just you, Y/N," he murmured. "Just you.”


End file.
